Epoxy resin compositions based on alkoxylated phenols

ABSTRACT

Epoxy-containing compounds are prepared by dehydrohalogenating the reaction product of an epihalohydrin with the reaction product of a compound containing an average of more than one aromatic hydroxyl group per molecule with an alkylene oxide wherein the ratio of moles of epihalohydrin to hydroxyl groups is at least about 1.2:1. When these epoxy containing compounds are formulated into coatings, the resultant products have improved chemical resistance to acids.

FIELD OF THE INVENTION

The present invention concerns epoxy resin compositions, curablecompositions containing same and cured products thereof.

BACKGROUND OF THE INVENTION

It would be desirable to have a liquid epoxy resin that providesincreased corrosion resistance, additional formulating time or pot-life,sprayable or paintable at ambient temperatures which maintains orexceeds the coating performance of conventional aromatic polyetherpolyepoxy resins.

Bowditch in U.S. Pat. No. 4,507,461 discloses epoxy resins prepared fromthe reaction of epichlorohydrin with the reaction product of a compoundcontaining aromatic hydroxyl groups and an alkylene oxide so as toproduce an aromatic compound containing aliphatic hydroxyl groups. Theepichlorohydrin is reacted in amounts which provides a stoichiometricexcess of 8 to 10 percent of the epichlorohydrin in relation to theequivalents of hydroxyl groups (this amounts to a ratio of moles ofepichlorohydrin per aliphatic hydroxyl group of from 1.08:1 to 1.1:1).These epoxy resins are useful as diluents for other epoxy resins and incoating compositions. While coatings can be prepared from mixtures ofthese epoxy resins disclosed by Bowditch and epoxy resins prepared fromepichlorohydrin and compounds having aromatic hydroxyl groups, theresultant coatings have less chemical resistance when coatingcompositions containing these epoxy resins are coated onto suchsubstrates as treated or untreated steel or treated or untreatedaluminum as compared to the chemical resistance of such substratescoated with like composition but without the epoxy resin disclosed byBowditch.

It would therefore be desirable to have available low viscosity epoxyresins which when blended with other epoxy resins and formulated into acoating composition would result in a coating which provides betterchemical resistance than that which is provided by the resins disclosedby Bowditch.

The present invention provides an epoxy resin which when blended withanother epoxy resin and formulated into a coating composition providescured coatings having an improvement in chemical resistance to acids. Inaddition, the present invention also provides a composition that allowsfor additional working time for the formulator resulting in greaterflexibility and control to the applicator.

SUMMARY OF THE INVENTION

One aspect of the present invention pertains to a product having anaverage of more than one vicinal epoxide group per molecule whichresults from dehydrohalogenating the product resulting from reacting

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; with

(2) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in component (1) is fromabout 1.2:1 to about 1.7:1.

Another aspect of the present invention pertains to a product having anaverage of more than one vicinal epoxide group per molecule whichresults from dehydrohalogenating the product resulting from reacting

(A) a mixture of

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; and

(2) at least one compound having an average of more than one aliphatichydroxyl group per molecule which compound is free of aromatic rings,wherein components (1) and (2) are present in amounts such that fromabout 40 to about 70 percent of the hydroxyl groups are contributed bycomponent (1) and from about 60 to about 30 percent of the hydroxylgroups are contributed by component (2), the percentages being basedupon the total amount of hydroxyl groups contributed by components (1)and (2); with

(B) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in components (A1) and (A2)is from about 1.08:1 to about 1.7:1.

Another aspect of the present invention pertains to an epoxy-containingcomposition which comprises a mixture of

(A) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; with

(2) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in component (1) is fromabout 1.2:1 to about 1.7:1; and

(B) at least one aromatic or cycloaliphatic based epoxy resin having anaverage of more than one vicinal epoxide group per molecule and havingan average degree of polymerization of from about 1 to about 14 or anycombination thereof.

Another aspect of the present invention pertains to an epoxy-containingcomposition which comprises a mixture of

(I) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(A) a mixture of

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; and

(2) at least one compound having an average of more than one aliphatichydroxyl group per molecule which compound is free of aromatic rings,wherein components (1) and (2) are present in amounts such that fromabout 30 to about 70 percent of the hydroxyl groups are contributed bycomponent (1) and from about 70 to about 30 percent of the hydroxylgroups are contributed by component (2) the percentages being based uponthe total amount of hydroxyl groups contributed by components (1) and(2); with

(B) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in components (A1) and (A2)is from about 1.08:1 to about 1.7:1; and

(II) at least one aromatic or cycloaliphatic based epoxy resin having anaverage of more than one vicinal epoxide group per molecule and havingan average degree of polymerization of from about 1 to about 14 or anycombination thereof.

Another aspect of the present invention pertains to a curablecomposition comprising

(A) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; with

(2) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in component (1) is fromabout 1.2:1 to about 1.7:1; and

(B) a curing amount of at least one curing agent or curing catalyst forcomponent (A).

Another aspect of the present invention pertains to a curablecomposition comprising

(I) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(A) a mixture of

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; and

(2) at least one compound having an average of more than one aliphatichydroxyl groups per molecule which compound is free of aromatic rings,wherein components (1) and (2) are present in amounts such that fromabout 30 to about 70 percent of the hydroxyl groups are contributed bycomponent (1) and from about 70 to about 30 percent of the hydroxylgroups are contributed by component (2) based on the total amount ofhydroxyl groups contained in components (1) and (2); with

(B) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in component (A1) and (A2) isfrom about 1.08:1 to about 1.7:1; and

(II) a curing amount of at least one curing agent or curing catalyst forcomponent (I).

Another aspect of the present invention pertains to a curablecomposition comprising

(A) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; with

(2) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in component (1) is fromabout 1.2:1 to about 1.7:1;

(B) at least one aromatic or cycloaliphatic based epoxy resin having anaverage of more than one vicinal epoxide group per molecule and havingan average degree of polymerization of from about 1 to about 14; and

(C) a curing amount of at least one curing agent or curing catalyst forcomponents (A) and (B).

Another aspect of the present invention pertains to a curablecomposition comprising

(I) a product having an average of more than one vicinal epoxide groupper molecule which results from dehydrohalogenating the productresulting from reacting

(A) a mixture of

(1) the product resulting from reacting

(a) at least one compound having an average of more than one aromatichydroxyl group per molecule; with

(b) at least one alkylene oxide having from 2 to about 4 carbon atomsper molecule in an amount which provides a ratio of moles of component(b) to aromatic hydroxyl groups contained in component (a) of from about1:1 to about 8:1; and

(2) at least one compound having an average of more than one aliphatichydroxyl groups per molecule which compound is free of aromatic rings,wherein components (1) and (2) are present in amounts such that fromabout 30 to about 70 percent of the hydroxyl groups are contributed bycomponent (1) and from about 70 to about 30 percent of the hydroxylgroups are contributed by component (2) based upon the total amount ofhydroxyl groups contributed by components (1) and (2); with

(B) at least one epihalohydrin wherein the ratio of moles ofepihalohydrin per hydroxyl group contained in components (A1) and (A2)is from about 1.08:1 to about 1.7:1;

(II) at least one aromatic or cycloaliphatic based epoxy resin having anaverage of more than one vicinal epoxide group per molecule and havingan average degree of polymerization of from about 1 to about 14; and

(III) a curing amount of at least one curing agent or curing catalystfor components (I) and (II).

Another aspect of the present invention pertains to the productresulting from curing the aforementioned curable compositions.

DETAILED DESCRIPTION OF THE INVENTION

An oxyalkylated aromatic compound is prepared by reacting at least onecompound having an average of more than one phenolic hydroxyl group permolecule with at least one alkylene oxide having from about 2 to about 4carbon atoms per molecule at a temperature suitably from about 140° C.to about 230° C., more suitably from about 150° C. to about 200° C.,most suitably from about 150° C. to about 190° C. for a time sufficientto complete the reaction, suitably from about 2 to about 48, moresuitably from about 2 to about 24, most suitably from about 4 to about20, hours.

At temperatures above about 230° C., undesired side reactions may takeplace or an uncontrollable reaction rate may be obtained resulting in apotentially hazardous condition.

At temperatures below about 140° C., the phenolic hydroxyl groups maynot melt and thus be difficult to mix and/or react in a uniform manner.

The reaction can be conducted at any suitable pressure which will keepthe more volatile reactants in liquid form at the reaction temperatureemployed. Atmospheric to superatmospheric pressures up to about 200 psia(1379 kPa) are usually employed. It is preferred to employ pressures offrom about 15 psia (103kPa) to about 100 psia (689 kPa).

The components are employed in amounts which provide a ratio of themoles of alkylene oxide per aromatic hydroxyl group of from about 1:1 toabout 8:1, from about 1:1 to about 4:1, more suitably from about 1.2:1to about 3:1, most suitably from about 1.25:1 to about 2.5:1.

At ratios of the moles of alkylene oxide per aromatic hydroxyl groupbelow about 1:1, unreacted aromatic hydroxyl groups remain which maycause processing problems and lower product yields.

At ratios above about 8:1, the final coating performance is lowered.

Suitable aromatic hydroxyl-containing compounds which can be employedherein include any compound containing an average of more than onearomatic hydroxyl group per molecule. Those compounds having twoaromatic hydroxyl groups per molecule such as dihydroxy benzene,biphenols and bisphenols are preferred. Suitable such compounds includethose represented by the following general formulas I, II or III##STR1## wherein each A is independently a divalent hydrocarbyl grouphaving suitably from 1 to about 12, more suitably from about 1 to about6, most suitably from 1 to about 4, carbon atoms, -S-, -S-S-, -SO-,SO2-, -0- or -CO-; each A' is independently a divalent hydrocarbyl group##STR2## having suitably from 1 to about 12, more suitably from about 1to about 6, most suitably from 1 to about 4, carbon atoms each X isindependently hydrogen, a hydrocarbyl or hydrocarbyloxy group havingsuitably from 1 to about 12, more suitably from about 1 to about 6, mostsuitably from 1 to about 4, carbon atoms, or a halogen, preferablychlorine or bromine; m has an average value suitably from 0.01 to about6, more suitably from about 0.01 to about 4, most suitably from about0.1 to about 4; and n has a value of zero or 1.

Particularly suitable aromatic hydroxylcontaining compounds include, forexample, resorcinol, hydroquinone, catechol, biphenol, bisphenol A(4,4'-isopropylidine diphenol), bisphenol K(4,4'-dihydroxybenzophenone), bisphenol S(4,4'-dihydroxydiphenylsulfone), bisphenol F(4,4'-dihydroxydiphenylmethane), bisphenol AP(4,4'-(1-phenylethylidene)diphenol), phenol-aldehyde novolac resins,particularly phenol-formaldehyde resins having an average functionalitysuitably from about 0.01 to about 6, more suitably from about 0.01 toabout 4, most suitably from about 0.1 to about 4.

Suitable alkylene oxides which can be employed to react with thearomatic hydroxyl-containing compound include, for example, ethyleneoxide, propylene oxide, butylene oxide, any combination thereof and thelike.

The resultant alkoxylated aromatic compound is then reacted with anepihalohydrin at a temperature suitably from about 50 to about 90, moresuitably from about 55 to about 80, most suitably from about 60 to about70 for a time sufficient to complete the reaction, suitably from about 1to about 6, more suitably from about 1 to about 4, most suitably fromabout 1.5 to about 3, hours at pressures from atmospheric tosuperatmospheric, usually up to about 100 psia (689 kPa), more suitablyfrom about 15 psia (103 kPa) to about 50 psia (344 kPa), most suitablyfrom about 15 psia (103 kPa) to about 30 psia (206 kPa) and thecomponents are employed in a ratio of moles of epihalohydrin perhydroxyl group contained in the above reaction product suitably fromabout 1.2 to about 1.7, more suitably from about 1.3 to about 1.7, mostsuitably from about 1.3 to about 1.5.

At temperatures above about 90° C, the reaction is difficult to controland has the possibility of having an uncontrollable exothermic reactionif heat energy cannot be removed efficiently.

At temperatures below about 50° C, the viscosity of the oxyalkylatedaromatic hydroxyl-containing compound may be too high to allow mixing ormixing may even be impossible.

At mole ratios below about 1.2:1, coatings prepared from thedehydrohalogenated product does not have the good acid resistanceproperty.

Suitable epihalohydrins which can be employed herein include, forexample, epichlorohydrin, epibromohydrin, epiiodohydrin,methylepichorohydrin, methylepibromohydrin, methylepiiodohydrin,ethylepichorohydrin, ethylepibromohydrin, ethylepiiodohydrin,propylepichorohydrin, propylepibromohydrin, propylepiiodohydrin,butylepichorohydrin, butylepibromohydrin, butylepiiodohydrin, anycombination thereof and the like.

If desired, before reacting the oxyalkylated aromatic compound with anepihalohydrin, it can be mixed with a compound having an average of morethan one aliphatic hydroxyl group per molecule which compound is free ofaromatic rings. Suitable such compounds having an average of more thanone aliphatic hydroxyl group per molecule and which is free of aromaticrings which can be employed herein, include, ethylene glycol, propyleneglycol, diethylene glycol, dipropylene glycol, tripropylene glycol,1,4-butanediol, 1,6-hexanediol, polyoxypropylene glycol, polyoxybutyleneglycol, glycerine, 1,2,3-trihydroxybutane, 1,2,4trihydroxybutane,trimethylol propane, neopentyl glycol, dibromoneopentyl glycol,cyclohexane dimethanol, any combination thereof and the like. While anyof the aliphatic hydroxyl-containing compounds free of aromatic ringsare suitable, it is preferred to employ those which are monomeric. i.e.those which are essentially free of ether groups. It is also preferredto employ those which have an average of more than two aliphatichydroxyl groups per molecule. These compounds can be blended in amountssuch that from about 30 to about 70, preferably from about 35 to about70, more preferably from about 40 to about 67 percent of the hydroxylgroups are contributed by the oxyalkylated aromatic compound and fromabout 70 to about 30, preferably from about 65 to about 30, morepreferably from about 60 to about 33, percent of the hydroxyl groups arecontributed by the aliphatic hydroxyl group-containing compound which isfree of aromatic rings, the percentages being based upon the totalamount of hydroxyl groups contributed by the hydroxyl group-containingcompounds.

When an epihalohydrin is reacted with such a mixture, it is employed inan amount which provides a ratio of moles of epihalohydrin per hydroxylgroup suitably from about 1.08:1 to about 1.7:1, more suitably fromabout 1.2:1 to about 1.7:1, most suitably from about 1.3:1 to about1.5:1.

At ratios below about 1.08:1, the resultant cured coating does not havethe desired improved acid resistance.

At ratios above about 1.7:1, the yield to desirable product may beundesirably decreased.

The reaction between the epihalohydrin and the alkoxylated aromaticcompound(s) or mixture of such compound(s) and aliphatichydroxyl-containing compound(s) is usually conducted in the presence ofa catalyst. Suitable such catalysts are Lewis acid catalysts. SuitableLewis acid catalysts include, for example, stannic chloride, borontrifluoride, boron trifluoride complexed with ethers or amines, anycombination thereof and the like so long as the catalyst does not causean undesired effect on the final epoxy resin. The catalyst is usuallyemployed in amounts of from about 0.002 to about 0.02, more usually fromabout 0.003 to about 0.018, most usually from about 0.003 to about0.016, mole of catalyst per hydroxyl equivalent.

Other processes are known that will couple epihalohydrin to an alcoholsuch as the process known as phase transfer catalysis. Suitablecatalysts that can be employed in this process include, for example,benzyltrimethyl ammonium chloride, benzyltriethyl ammonium chloride,benzyltrimethyl ammonium hydroxide, tetrabutyl ammonium chloride, andthe like.

In the phase transfer method, the quantity of catalyst varies with thereactants, catalyst and reaction conditions, however the catalyst can beemployed in amounts of from about 0.5 to about 7; more suitably fromabout 1 to about 6; most suitable from about 2 to about 5, percent byweight of catalyst based on the weight of hydroxyl-containing compoundemployed.

The product resulting from reacting the epihalohydrin with the aliphatichydroxyl-containing compound or compounds is then dehydrohalogenatedwith a basic acting compound to form the vicinal epoxycontainingcompound. Suitable basic acting compounds which can be employed hereinas the dehydrohalogenating agent include, for example, alkali metal andalkaline earth metal hydroxides, combinations thereof and the like.Preferred dehydrohalogenating agents are the alkali metal hydroxides,particularly sodium hydroxide. The dehydrohalogenating agents areemployed in amounts which provide from about 0.97 to about 3, moresuitably from about 1 to about 2, most suitably from about 1 to about1.6 moles of dehydrohalogenating agent per halohydrin group contained inthe reaction product resulting from reacting the oxyalkylated aromaticcompound or mixture of oxyalkylated aromatic compound and compoundhaving an average of more than two aliphatic hydroxyl groups permolecule.

At amounts less than about 0.97 mole of dehydrohalogenating agent perhalohydrin group incomplete reaction will occur causing decreasedproduct yields.

At amounts more than about 3 moles of dehydrohalogenating agent perhalohydrin group the possibility for oligomer formation is increasedwhich results in potentially decreased product yields.

The resultant epoxy compounds can be blended with aromatic orcycloaliphatic based epoxy resins having an average degree ofpolymerization of from about 1 to about 14, more suitably from about 1to about 6, most suitably from about 1 to about 3, and an averagefunctionality of from greater than 1 to about 3, preferably from about1.5 to about 2.2, more preferably from about 1.75 to about 2.1.

By degree of polymerization, it is meant the average number ofrepeatable groups plus 1 present in the epoxy resin.

For purposes of further clarification of what is meant by degree ofpolymerization, in Formulas IV to IX enumerated below, when m' and n'have values of zero, the epoxy resin has a degree of polymerization of1; likewise, when they have average values of 0.1, 0.5, 1, 2, etc., thedegree of polymerization is 1.1, 1.5, 2, 3, etc.

What is meant by the term aromatic or cycloaliphatic based epoxy resins,it is meant that the glycidyl ether group is attached to a carbon atomin an aromatic or benzene ring or a cycloaliphatic ring.

Suitable such aromatic or cycloaliphatic based epoxy resins which can beemployed herein include, for example, those represented by the followingFormulas IV, V, VI, VII, VIII or IX ##STR3## wherein each A isindependently a divalent hydrocarbyl ##STR4## group having suitably from1 to about 12, more suitably from about 1 to about 6, more suitably from1 to about 4, carbon atoms, -S-, -S-S-, -SO-, SO₂ -, -0- or -CO-; eachA' is independently a divalent hydrocarbyl group having suitably from 1to about 12, more suitably from about 1 to about 6, most suitably from 1to about 4, carbon atoms; each R is independently hydrogen or an alkylgroup having from 1 to about 4 carbon atoms; each X is independentlyhydrogen, a hydrocarbyl or hydrocarbyloxy group having suitably from 1to about 12, more suitably from about 1 to about 6, most suitably from 1to about 4, carbon atoms, or a halogen, preferably chlorine or bromine;m' has an average value suitably from 0.01 to about 6, more suitablyfrom about 0.01 to about 4, most suitably from about 0.1 to about 4; nhas a value of zero or 1; and n' has an average value suitably fromabout zero to about 13, more suitably from zero to about 5, mostsuitably from zero to about 2.

Particularly suitable epoxy resins which can be blended with the otherepoxy-containing compounds include, for example, the diglycidyl ethersof biphenol, bisphenol A, bisphenol F, bisphenol K, bisphenol S,bisphenol AP, hydrogenated biphenol, hydrogenated bisphenol A,hydrogenated bisphenol F, hydrogenated bisphenol K, hydrogenatedbisphenol S, hydrogenated bisphenol AP; polyglycidyl ethers of phenol-or cyclohexanol-aldehyde novolac resins, combinations thereof and thelike.

The blends suitably contain from about 20 to about 80, more suitablyfrom about 30 to about 70, most suitably from about 35 to about 65,percent by weight glycidyl ether of aliphatic hydroxyl-containingcompound(s) and from about 80 to about 20, more suitably from about 70to about 30, most suitably from about 65 to about 35, percent by weightaromatic or cycloaliphatic based epoxy resin all percentages being basedupon the combined weight of the epoxy-containing compounds.

The epoxy-containing compounds can be cured with any suitable curingagent or curing catalyst. Suitable such curing agents or curingcatalysts are disclosed by Lee and Neville in Handbook of Epoxy Resins,McGraw-Hill, (1967), in EPOXY RESINS Chemistry and Technology, Edited byClayton A. May, Marcel Dekker, Inc. (1988), both of which areincorporated herein by reference. Suitable such curing agents include,for example, primary and secondary aliphatic, cycloaliphatic or aromaticamines, polyalkylene polyamines, polycarboxylic acids and anhydridesthereof, polysulfides, compounds having a plurality of aromatic hydroxylgroups, polyamides, guanidines, biguanides, combinations thereof and thelike. Particularly suitable curing agents include, for example,ethylenediamine, 1,3-prpanediamine, 1,6-hexanediamine,diethylenetriamine, triethylenetetramine, 1,3-diaminocyclohexane,N-aminoethylpiperazine, 4,4'-methylenedianiline, diaminodiphenylsulfone,amidoamines obtained from the reaction of fatty acids with polyamines,aminated polypropylene glycol, polyamine adducts of the diglycidyl etherof bisphenol A, polyamine adducts of the diglycidyl ether of bisphenolF, dicyanidamide, phthalic anhydride, terephthalic acid, NADIC methylanhydride, any combination thereof and the like.

The following examples are illustrative of the present invention, butare not to be construed as to limiting the scope thereof in any manner.

The following components are employed in the examples.

ALCOHOL A is a dialcohol of the reaction product of about 3.4 moles ofpropylene oxide with about 1 mole of bisphenol A resulting in a hydroxylequivalent weight (HEW) of 214.1.

ALCOHOL B is trimethanol propane having a HEW of 44.7.

ALCOHOL C is a dialcohol of the reaction product of about 4 moles ofbutylene oxide with about 1 mole of bisphenol A resulting in a HEW of268.1.

EPOXY RESIN A is a diglycidyl ether of bisphenol A having an epoxyequivalent weight (EEW) of 171.7.

EPOXY RESIN B is a diglycidyl ether of bisphenol A having an EEW of 172that has been reacted with 0.0233 equivalent of pelargonic acid, 0.018equivalent of lauric acid and 0.016 equivalent of myristic acidresulting in an epoxy resin having an EEW of 198.

AMINE A is an amine available from Henkel Corp. as GENAMID 235 having anamine hydrogen equivalent weight (AHEW) of 95.

AMINE B is a curing agent containing aliphatic primary and secondaryamine groups available from The Dow Chemical Company as D.E.H.™ 52 EpoxyHardener having an AHEW of 44.5.

EXAMPLE 1 A. Mole Ratio of Epihalohydrin to OH Groups of 1.152:1 (Not anExample of the Present Invention)

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 400 gms (1.8683 alcoholequiv.) of ALCOHOL A and 7.48 gms (0.0287 mole) of stannic chloride at50° C. The temperature of the mixture is increased to 60° C. whereupon199.08 gm (2.1522 moles) of epichlorohydrin is added over a time periodof 1.58 hours. After the epichlorohydrin addition is complete, thereaction mixture is digested for 0.75 hours at 65° C. Methyl isobutylketone, 400 gms, is added and at a temperature of 85° C. add 95.6 gms ofwater and 95.6 gms of 50 weight percent sodium hydroxide. Thetemperature decreases to 56° C. Heat the reaction mixture to 85° C. andmaintain for 2.67 hours then let the two phases separate. Remove theaqueous phase and add 78 gms of water and 78 gms of 50 weight percentsodium hydroxide. Increase the temperature to 85° C. and maintain for 2hours. Let the two phases separate then remove the aqueous phase. Repeatthe previous step. After the separation, add 1400 gms of methyl isobutylketone and wash the organic phase with water to a neutral pH. Thiswashing step employs three water treatments of 600 gms of water eachtime. The resulting solution is vacuum distilled to remove the solventand residual water yielding 491 gms of product. The resulting productgives a percent epoxide of 12.36, percent total chloride of 2.76 and ahydrolyzable chloride of 109 ppm.

B. Mole Ratio of Epihalohydrin to OH Groups of 1.286:1

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 527.9 gms (2.4657 OH equiv.)of ALCOHOL A and 3.0 gms (0.0115 mole) of stannic chloride at 30° C. Thetemperature of the mixture is increased to 60° C. whereupon 293.4 gm(3.1719 moles) of epichlorohydrin is added over a time period of 1.17hours. After the epichlorohydrin addition is complete, the reactionmixture is digested for 0.75 hours at 65° C. Methyl isobutyl ketone, 548gms, is added and at a temperature of 85° C. add 130 gms of water and130 gms of 50 weight percent sodium hydroxide. The temperature decreasesto 70° C. Heat the reaction mixture to 85° C. and maintain for 1.98hours then let the two phases separate. Remove the aqueous phase thenadd 120 gms of water and 120 gms of 50 weight percent sodium hydroxide.Increase the temperature to 85° C. and maintain for 2 hours. Let the twophases separate then remove the aqueous phase. After the separation, add1916 gms of methyl isobutyl ketone and wash the organic phase with waterto a neutral pH. This washing step employs three water treatments of 800gms of water each time. The resulting solution is vacuum distilled toremove the solvent and residual water yielding 763.8 gms of product. Theresulting product gives a percent epoxide of 12.82, percent totalchloride of 4.1 and a hydrolyzable chloride of 48 ppm.

C. Mole Ratio of Epihalohydrin to OH Groups of 1.5:1

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 464.7 gms (2.1705 alcoholequiv.) of ALCOHOL A and 5.0 gms (0.0192 mole) of stannic chloride at24° C. The temperature of the mixture is increased to 60° C. whereupon301.2 gm (3.2562 moles) of epichlorohydrin is added over a time periodof 1.03 hours maintaining a temperature between 60° C. to 80° C. Afterthe epichlorohydrin addition is complete, the reaction mixture isdigested for 0.75 hours at 60° C. Methyl isobutyl ketone, 510.5 gms, isadded and at a temperature of 80° C. add 130 gms of water and 130 gms of50 weight percent sodium hydroxide. Heat reaction mixture of 80° C. andmaintain for 2 hours then let the two phrases separate. Remove theaqueous phase then add 130 gms of water and 130 gms of 50 weight percentsodium hydroxide. Increase the temperature to 80° C. and maintain for1.98 hours. Let the two phases separate then remove the aqueous phasethen add 130 gms of water and 130 gms of 50 weight sodium hydroxide.Increase the temperature to 80° C. and maintain for 3.08 hours. Let thetwo phases separate then remove the aqueous phase. After the separation,add 1787 gms of methyl isobutyl ketone and wash the organic phase withwater to a neutral pH. This washing step employs three water treatmentsof 766 gms of water each time. The resulting solution is vacuumdistilled to remove the solvent and residual water. The resultingproduct gives a percent epoxide of 12.97, percent total chloride of 5.49a hydrolyzable chloride of 36 ppm.

D Mole Ratio of Epihalohydrin to OH Groups of 1.7:1

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 464.7 gms (2.1705 alcoholequiv.) of ALCOHOL A and 5.0 gms (0.0192 mole) of stannic chloride at27° C. The temperature of the mixture is increased to 60° C. whereupon341.3 gm (3.6897 moles) of epichlorohydrin is added over a time periodof 1.08 hours. After the epichlorohydrin addition is complete, thereaction mixture is digested for 0.75 hours at 60° C. Methyl isobutylketone, 537 gms, is added and at a temperature of 80° C. add 148 gms ofwater and 148 gms of 50 weight percent sodium hydroxide. The temperaturedecreases to 68° C. Heat the reaction mixture to 80° C. and maintain for2 hours then let the two phases separate. Remove the aqueous phase thenadd 148 gms of water and 148 gms of 50 weight percent sodium hydroxide.Increase the temperature to 80° C. and maintain for 2 hours. Let the twophases separate then remove the aqueous phase then add 148 gms of waterand 148 gms of 50 weight percent sodium hydroxide. Increase thetemperature to 80° C. and maintain for 3 hours. Let the two phasesseparate then remove the aqueous phase. After the separation, add 1881gms of methyl isobutyl ketone and wash the organic phases with water toa neutral pH. This washing step employs three water treatments of 800gms of water each time. The resulting solution is vacuum distilled toremove the solvent and residual water. The resulting product gives apercent epoxide of 12.71, percent total chloride of 6.89 andhydrolyzable chloride of 3 ppm.

EXAMPLE 2 (Mixture of Aliphatic OH Compounds; 65.15% of OH GroupsContributed by Oxyalkylated Aromatic Compound; Mole Ratio ofEpihalohydrin:OH of 1.289:1)

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 315 gms (1.4713 alcoholequiv.) of ALCOHOL A, 35 gms (0.7829 alcohol equiv.) of ALCOHOL B, and2.6 gms (0.0099 mole) of stannic chloride at ambient temperature. Thetemperature of the mixture is increased to 60° C. whereupon 268.7 gm(2.9048 moles) of epichlorohydrin is added over a time period of 0.9hour. After the epichlorohydrin addition is complete, the reactionmixture is digested for 0.75 hours at 65° C. Methyl isobutyl ketone,412.5 gms, is added and at a temperature of 58° C. add 230 gms of waterand 230 gms of 50 weight percent sodium hydroxide. Heat the reactionmixture to 85° C. and maintain for three hours then let the two phasesseparate. Remove the aqueous phase and add 120 gms of water and 120 gmsof 50 weight percent sodium hydroxide. Increase the temperature to 85°C. and maintain for 2 hours. Let the two phases separate then remove theaqueous phase. After the separation, add 1443.6 gms of methyl isobutylketone and wash the organic phase with water to a neutral pH. Thiswashing step employs eight water treatments of 600 gms of water eachtime. The resulting solution is vacuum distilled to remove the solventand residual water yielding 573 gms of product. The resulting productgives a percent epoxide of 15.74, percent total chloride of 4.49 and ahydrolyzable chloride of 195 ppm.

EXAMPLE 3 (Mixture of Aliphatic OH Compounds; 45.38% of OH GroupsContributed by Oxyalkylated Aromatic Compound; Mole Ratio ofEpihalohydrin:OH of 1.303:1)

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 320 gms (1.4946 alcoholequiv.) of ALCOHOL A, 80 gms (1.7897 alcohol equiv.) of ALCOHOL B, and3.3 gms (0.0127 mole) of stannic chloride at ambient temperature. Thetemperature of the mixture is increased to 60° C. whereupon 395 gm(4.2703 moles) of epichlorohydrin is added over a time period of 1.58hour. After the epichlorohydrin addition is complete, the reactionmixture is digested for 0.75 hours at 65° C. Methyl isobutyl ketone, 530gms, is added and at a temperature of 75° C. add 345 gms of water and345 gms of 50 weight percent sodium hydroxide. Heat the reaction mixtureto 70° C. and maintain for three hours then let the two phases separate.Remove the aqueous phase and add 170 gms of water and 170 gms of 50weight percent sodium hydroxide. Increase the temperature to 85° C. andmaintain for 1.92 hour. Let the two phases separate then remove theaqueous phase. After the separation, add 1855 gms of methyl isobutylketone and wash the organic phase with water to a neutral pH. Thiswashing step employs ten water treatments of 800 gms of water each time.The resulting solution is vacuum distilled to remove the solvent andresidual water yielding 723 gms of product. The resulting product givesa percent epoxide of 18.57, percent total chloride of 5.71 and ahydrolyzable chloride of 205 ppm.

EXAMPLE 4 (Mole Ratio of Epihalohydrin:OH of 1.291:1)

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 449 gms (1.6747 alcoholequiv.) of ALCOHOL C and 4.9 gms (0.0188 mole) of stannic chloride atambient temperature. The temperature of the mixture is increased to 60°C. whereupon 200 gm (2.1622 moles) of epichlorohydrin is added over atime period of 0.6 hour. After the epichlorohydrin addition iscompleted, the reaction mixture is digested for 0.73 hours at 65° C.Methyl isobutyl ketone, 430 gms, is added and at a temperature of 64° C.add 99 gms of water and 99 gms of 50 weight percent sodium hydroxide.Heat the reaction mixture to 85° C. and maintain for three hours thenlet the two phases separate. Remove the aqueous phase and add 81 gms ofwater and 81 gms of 50 weight percent sodium hydroxide. Increase thetemperature to 85° C. and maintain for 2 hours. Let the two phasesseparate then remove the aqueous phase. Remove the aqueous phase and add81 gms of water and 81 gms of 50 weight percent sodium hydroxide.Increase the temperature to 85° C. and maintain for 2.3 hours. Let thetwo phases separate then remove the aqueous phase. Repeat the last stepone more time. After the separation, add 1500 gms of methyl isobutylketone and wash the organic phase with water to a neutral pH. Thiswashing step employs three water treatments of 600 gms of water eachtime. The resulting solution is vacuum distilled to remove the solventand residual water yielding 608 gms of product. The resulting productgives a percent epoxide of 11.01, percent total chloride of 3.62 and ahydrolyzable chloride of 70 ppm.

EXAMPLE 5

The gelation time is determined by mixing the epoxy resins with theamines at an equivalent ratio of 1:1 giving a total of 100 gms. Theresults are shown in Table I.

                  TABLE I                                                         ______________________________________                                        (Cure Time)                                                                                                    Cure                                                                          Time                                                 Curing      Epoxy Resin  in                                           Sample    Agent   Type       Grams Hours                                      ______________________________________                                        A*        Amine   1A         88.42  6.06                                                B                                                                   B         Amine   1B         88.25 16.38                                                B                                                                   ______________________________________                                         *Not an example of the present invention.                                

EXAMPLE 6

Coating formulations are prepared from some of the epoxy compositionsprepared above and tested for gloss and corrosion (chemical) resistance.The coating formulations are prepared by adding the epoxy resins to aone quart (0.946 1) metal container, adding the fillers, additives andsolvents. After blending the mixture, the curing agent is added andblended. The resultant coating is then applied to a cold rolled steelsubstrate using a pull-down-bar to a wet film thickness of 6 mils(0.1524 mm). The coated panels are then cured at ambient temperature forseven days.

The resultant cured panels are then tested for Chemical Resistance Thecoated cold rolled steel panel is prepared for testing in the followingmanner.

A rubber gasket measuring 63 mm O.D.×38 mm I.D.×3 mm long is affixed tothe pigmented coating surface using a rubberized cement. This is allowedto set, then the test acid is placed inside the cut-out gasket coveringthe exposed coating surface. A glass cover is then placed on top of thegasket and sealed with high viscosity grease. The appearance of thecoating is viewed through the glass cover to determine when the coatingfailure occurs. A coating failure occurs when the coating begins todelaminate or bubbles or blisters are noted.

The formulation and results are given in Table II.

                                      TABLE II                                    __________________________________________________________________________    Component &                                                                            Sample Designation                                                   Property A*     B      C      D                                               __________________________________________________________________________    Epoxy Resin                                                                   Type/grams                                                                             B/50   B/50   B/50   B/50                                            Type/grams                                                                             Ex 1A/50                                                                             Ex 1B/50                                                                             Ex 2/50                                                                              Ex 3/50                                         Amine B, gms.                                                                          17.64  18.02  19.52  20.99                                           TiO.sub.2, gms.                                                                        86.6   86.6   86.6   86.6                                            BaSO.sub.4, gms.                                                                       200    200    200    200                                             Bentone SD-3.sup.a,                                                                    3      3      3      3                                               gms.                                                                          BYK 310.sup.b, gms.                                                                    1.5    1.5    1.5    1.5                                             BYK 052.sup.c, gms.                                                                    1.5    1.5    1.5    1.5                                             Methyl Isobutyl                                                                        10.16  10.64  9.84   9.28                                            Ketone, gms.                                                                  Methyl Ethyl                                                                           20.32  21.28  19.68  18.56                                           Ketone, gms.                                                                  Butanol, gms.                                                                          33.02  34.58  31.98  30.16                                           Corrosion                                                                              5      7      5      5                                               Resist.                                                                       to HNO.sub.3, time to                                                         failure in days                                                               Corrosion                                                                              2.40   2.64   3.60   7.92                                            Resist.                                                                       to Glacial                                                                    Acetic Acid,                                                                  time to failure                                                               in hours                                                                      __________________________________________________________________________     *Not an example of the present invention.                                     .sup.a Bentone SD3 is an organoclay commercially available from NL            Industries employed as a rheological control additive.                        .sup.b BYK310 is a heat resistance silicone additive commercially             available from BYK Chemie employed to improve leveling, increased surface     slip, reduced cratering and prevent Benart cell formation.                    .sup.c BYK 052 is a defoamer additive commercially available from BYK         CHemie.                                                                  

EXAMPLE 7 Mole Ratio of Epihalohydrin to OH Groups of 1.1:1 with 10%ALCOHOL B

To a reaction vessel equipped with a nitrogen purge, stirrer,temperature control and condenser is added 489.6 gms (2.2868 alcoholequiv.) of ALCOHOL A, 54.4 gms (1.217 alcohol equiv.) of ALCOHOL B, and6 gms (0.0228 mole) of stannic chloride at 60° C. whereupon 356.5 gm(3.8541 moles) of epichlorohydrin is added over a time period of 1.75hours. After the epichlorohydrin addition is complete, the reactionmixture is digested for 0.75 hour at 65° C. Methyl isobutyl ketone,600.4 gms, is added and after raising the temperature to 80° C., 308 gmsof water and 308 gms of 50 weight percent sodium hydroxide are added.The temperature of 80° C. is maintained for 3.07 hours. The reactionmixture is then allowed to separate into two phases. The aqueous phaseis removed and 154 gms of water and 154 gms of weight percent sodiumhydroxide are added. The temperature is increased to 80° C. andmaintained for 2 hours. The reaction mixture is allowed to separate intotwo phases and the aqueous phase removed . After the separation, 2101gms of methyl isobutyl ketone are added and the organic phase is washedwith water to a neutral pH. This washing step employs three watertreatments of 890 gms of water each time. The resulting solution isvacuum distilled to remove the solvent. The resulting product gives apercent epoxide of 5.27, percent total chloride of 0.33 and ahydrolyzable chloride of 1 ppm.

COATING RESULTS

Coatings are prepared by blending the components listed in the followingTable III.

                  TABLE III                                                       ______________________________________                                                                       Curing Agent                                   Sample   Resin 1      Resin 2  (DEH 58)                                       Number   (gms)        (gms)    (gms)                                          ______________________________________                                        A*       30 gms of    0        2.57                                                    Example 1A                                                           B        30 gms of    0        2.65                                                    Example 1B                                                           C*       15 gms of    15.2 gms 3.92                                                    Example 1A   Epoxy                                                                         Resin A                                                 D        15 gms of    15.3 gms 3.97                                                    Example 1B   Epoxy                                                                         Resin A                                                 ______________________________________                                         *Not an example of the present invention.                                

Samples A and B are allowed to stand at ambiet temperature (25° C.) for1.25 hours and Samples C and D are allowed to stand at ambiettemperature at 25° C. for .25 hour prior to coating onto 4"×12"×24 guage(101.6 mm×304,8 mm×0.63 mm) untreated cold rolled steel panels. Thepanels are cured at ambient temperature for three (3) days prior totesting.

Chemical resistance is determined using the unpigmented panels coatedwith the unpigmented coating formulations after curing. To the cured,coated panel is placed about 1-2 ml of glacial acetic acid and a timerstarted. The coating is observed for delamination, bubbles or blisters.The surface is maintained wet with glacial acetic acid by the additionof more acid as needed. The results are given in the following Table IV.

                  TABLE IV                                                        ______________________________________                                                                Glacial                                                                       Acetic                                                                        Acid                                                  Sample        Thickness Resistance                                            Number        (Mil/mm)  (sec)                                                 ______________________________________                                        A*            0.72/0.018                                                                              107                                                   B             0.83/0.021                                                                              177                                                   C*            1.83/0.046                                                                              246                                                   D             2.10/0.053                                                                              337                                                   ______________________________________                                         *Not an example of the present invention.                                

Samples A and B are allowed to stand at ambiet temperature (25° C.) for1.25 hours and Samples C and D are allowed to stand at ambiettemperature at 25° C. for .25 hour prior to coating onto 4"×12"×24 guage(101.6 mm×304,8 mm×0.63 mm) untreated cold rolled steel panels. Thepanels are cured at ambient temperature for seven (7) days prior totesting. These cured, coated panels are then tested for chemicalresistance (glacial acetic acid) accoring to the above describedprocedure. The results are given in the following Table V.

                  TABLE V                                                         ______________________________________                                                                Glacial                                                                       Acetic                                                                        Acid                                                  Sample        Thickness Resistance                                            Number        (mil/mm)  (sec)                                                 ______________________________________                                        A             1.68/0.043                                                                              182                                                   B             1.68/0.043                                                                              243                                                   C             1.61/0.041                                                                               84                                                   B             1.79/0.045                                                                              263                                                   ______________________________________                                         *Not an example of the present invention.                                

Pigmented coatings are prepared and tested by the procedure described inexample 6. The coating formulations and test results after curing thecoated panels for 14 days at ambient temperature are given in Table VI.

                                      TABLE VI                                    __________________________________________________________________________    Component                                                                              Sample Number                                                        & Property                                                                             A*    B     C     D     E                                            __________________________________________________________________________    Epoxy                                                                         Resin                                                                         Type/grams                                                                             B/50  B/50  A/50  A/60  A/40                                         Type/grams                                                                             Ex 1A/50                                                                            Ex 1B/50                                                                            Ex 1B/50                                                                            Ex 1B/40                                                                            Ex 1B/60                                     Amine B, 17.64 17.94 19.71 20.95 18.45                                        gms.                                                                          TiO2, gms.                                                                             75.9  75.9  75.9  75.9  75.9                                         BaSO4,   175.4 175.4 175.4 175.4 175.4                                        gms.                                                                          Bentone  3     3     3     3     3                                            SD-3, gms.                                                                    BYK 310, 1.5   1.5   1.5   1.5   1.5                                          gms.                                                                          BYK 052, 1.5   1.5   1.5   1.5   1.5                                          gms.                                                                          Methyl   10.16 10.16 10.16 10.16 10.16                                        Isobutyl                                                                      Ketone,                                                                       gms.                                                                          Methyl   20.32 20.32 20.32 20.32 20.32                                        Ethyl                                                                         Kentone,                                                                      gms.                                                                          Butanol, 33.02 33.02 33.02 33.02 33.02                                        gms.                                                                          Corrosion                                                                              0.25  0.45  0.68  1.33  0.3                                          Resis to                                                                      Glacial                                                                       Acetic                                                                        Acid,                                                                         failure in                                                                    hour                                                                          __________________________________________________________________________    Component                                                                              Sample No.                                                           & Property                                                                             F     G     H     I     J                                            __________________________________________________________________________    Epoxy                                                                         Resin                                                                         Type/grams                                                                             B/50  B/50  B/50  B/50  B/50                                         Type/grams                                                                             Ex 1C/50                                                                            Ex 1D/50                                                                            Ex 2/50                                                                             Ex 3/50                                                                             Ex 7/50                                      Amine B, 17.9  17.80 19.32 20.8  13.9                                         gms.                                                                          TiO2, gms.                                                                             75.9  75.9  75.9  785.9 875.9                                        BaSO4,   175.4 175.4 175.4 175.4 175.4                                        gms.                                                                          Bentone  3     3     3     3     3                                            SD-3, gms.                                                                    BYK 310, 1.5   1.5   1.5   1.5   1.5                                          gms.                                                                          BYK 052, 1.5   1.5   1.5   1.5   1.5                                          gms.                                                                          Methyl   10.16 10.16 10.16 10.16 10.16                                        Isobutyl                                                                      Ketone,                                                                       gms.                                                                          Methyl   20.32 20.32 20.32 20.32 20.32                                        Ethyl                                                                         Kentone,                                                                      gms.                                                                          Butanol, 33.02 33.02 33.02 33.02 33.02                                        gms.                                                                          Corrosion                                                                              0.37  0.53  1.53  1.17  0.17                                         to Glacial                                                                    Acetic                                                                        Acid,                                                                         failure in                                                                    hour                                                                          __________________________________________________________________________     *Not an example of the present invention.                                

What is claimed is:
 1. An epoxy-containing composition which comprises a mixture of(I) a product having an average of more than one vicinal epoxide group per molecule which results from dehydrohalogenating the product resulting from reacting(A) a mixture of(1) the product resulting from reacting(a) at least one compound having an average of more than one aromatic hydroxyl group per molecule; with (b) at least one alkylene oxide having from 2 to about 4 carbon atoms per molecule in an amount which provides a ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) of from about 1:1 to about 8:1; and (2) at least one compound having an average of more than one aliphatic hydroxyl group per molecule which compound is free of aromatic rings, wherein components (1) and (2) are present in amounts such that from about 30 to about 70 percent of the hydroxyl groups are contributed by component (1) and from about 70 to about 30 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); with (B) at least one epihalohydrin wherein the ratio of moles of epihalohydrin per hydroxyl group contained in components (1) and )2) is from about 1.08:1 to about 1.7:1; and (II) at least one aromatic or cycloaliphatic epoxy resin having an average of more than one vicinal epoxide group per molecule and having a degree of polymerization of from about 1 to about
 14. 2. A composition of claim 1 wherein(i) in component (IA1), the ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) is from about 1.2:1 to about 3:1; (ii) in component (IA), components (1) and (2) are present in amounts such that from about 35 to about 70 percent of the hydroxyl groups are contributed by component (1) and from about 65 to about 30 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); (iii) the ratio of moles of epihalohydrin per hydroxyl group contained in components (IA1) and (IA2) is from about 1.2:1 to about 1.7:1; and (iv) component (II) is employed in an amount of from about 20 to about 80 percent by weight based upon the combined weight of components (I) and (II).
 3. A composition of claim 1 wherein(i) in component (1), the ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) is from about 1.25:1 to about 2.5:1; (ii) in component (A), components (1) and (2) are present in amounts such that from about 40 to about 67 percent of the hydroxyl groups are contributed by component (1) and from about 60 to about 33 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); (iii) the ratio of moles of epihalohydrin per hydroxyl group contained in components (A1) and (A2) is from about 1.3:1 to about 1.5:1; and (iv) component (II) is employed in an amount of from about 30 to about 70 percent by weight based upon the combined weight of components (I) and (II).
 4. A composition of claim 1, 2 or 3 wherein(i) component (A1a) is a biphenol or a bisphenol compound; (ii) component (A1b) is ethylene oxide, 1,2propylene oxide or 1,2-butylene oxide; (iii) component (A2) is a compound containing an average of more than two aliphatic hydroxyl groups per molecule; and (iv) component (II) is a diglycidyl ether of a biphenol or a bisphenol compound having a degree of polymerization of from about 1 to about 6 or any combination of such diglycidyl ethers.
 5. A composition of claim 1, 2 or 3 wherein(i) component (A1a) is bisphenol A, bisphenol F, bisphenol K, bisphenol S, bisphenol AP or any combination thereof; (ii) component (A1b) is 1,2-propylene oxide; (iii) component (A2) is glycerine, trimethylolpropane, or any combination thereof; (iv) component (B) is epichlorohydrin; and (v) component (II) is a diglycidyl ether of bisphenol A, bisphenol F, bisphenol K, bisphenol S, or bisphenol AP having a degree of polymerization of from about 1 to about 3 or any combination thereof.
 6. A curable composition comprising(I) a product having an average of more than one vicinal epoxide group per molecule which results from dehydrohalogenating the product resulting from reacting(A) a mixture of(1) the product resulting from reacting(a) at least one compound having an average of more than one aromatic hydroxyl group per molecule; with (b) at least one alkylene oxide having from 2 to about 4 carbon atoms per molecule in an amount which provides a ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) of from about 1:1 to about 8:1; and (2) at least one compound having an average of more than one aliphatic hydroxyl group per molecule which compound is free of aromatic rings, wherein components (1) and (2) are present in amounts such that from about 30 to about 70 percent of the hydroxyl groups are contributed by component (1) and from about 70 to about 30 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); with (B) at least one epihalohydrin wherein the ratio of moles of epihalohydrin per hydroxyl group contained in components (A1) and (A2) is from about 1.08:1 to about 1.7:1; (II) at least one aromatic or cycloaliphatic epoxy resin having an average of more than one vicinal epoxide group per molecule and having a degree of polymerization of from about 1 to about 14; and (III) a curing amount of at least one curing agent or curing catalyst for components (I) and (II).
 7. A curable composition of claim 6 wherein(i) in component (IA1), the ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) is from about 1.2:1 to about 3:1; (ii) in component (IA), components (1) and (2) are present in amounts such that from about 35 to about 70 percent of the hydroxyl groups are contributed by component (1) and from about 65 to about 30 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); (iii) the ratio of moles of epihalohydrin per hydroxyl group contained in components (IA1) and (IA2) is from about 1.2:1 to about 1.7:1; and (iv) component (II) is employed in an amount of from about 20 to about 80 percent by weight based upon the combined weight of components (I) and (II).
 8. A curable composition of claim 6 wherein(i) in component (1), the ratio of moles of component (b) to aromatic hydroxyl groups contained in component (a) is from about 1.25:1 to about 2.5:1; (ii) in component (A), components (1) and (2) are present in amounts such that from about 40 to about 67 percent of the hydroxyl groups are contributed by component (1) and from about 60 to about 33 percent of the hydroxyl groups are contributed by component (2) the percentages being based upon the total amount of hydroxyl groups contributed by components (1) and (2); (iii) the ratio of moles of epihalohydrin per hydroxyl group contained in components (A1) and (A2) is from about 1.3:1 to about 1.5:1; and (iv) component (II) is employed in an amount of from about 30 to about 70 percent by weight based upon the combined weight of components (I) and (II).
 9. A curable composition of claim 6, 7 or 8 wherein(i) component (A1a) is a biphenol or a bisphenol compound; (ii) component (A1b) is ethylene oxide, 1,2propylene oxide or 1,2-butylene oxide; (iii) component (A2) is a compound containing an average of more than two aliphatic hydroxyl groups per molecule; (iv) component (II) is a diglycidyl ether of a biphenol or a bisphenol compound having a degree of polymerization of from about 1 to about 6 or any combination of such diglycidyl ethers; and (v) component (III) is an aliphatic or aromatic polyamine, polyamide, polysulfide, a polycarboxylic acid or anhydride thereof, a compound containing a plurality of aromatic hydroxyl groups, or any combination thereof.
 10. A curable composition of claim 6, 7 or 8 wherein(i) component (A1a) is bisphenol A, bisphenol F, bisphenol K, bisphenol S, bisphenol AP or any combination thereof; (ii) component (A1b) is 1,2-propylene oxide; (iii) component (A2) is glycerine, trimethylolpropane, or any combination thereof; (iv) component (B) is epichlorohydrin; (v) component (II) is a diglycidyl ether of bisphenol A, bisphenol F, bisphenol K, bisphenol S, or bisphenol AP having a degree of polymerization of from about 1 to about 3 or any combination thereof; and (vi) component (III) is a polyalkylene polyamine, an amidoamine prepared by reacting at least one fatty acid with at least one polyamine, or any combination thereof.
 11. The product resulting from curing the curable composition of claim 6, 7, or
 8. 12. The product resulting from curing the curable composition of claim
 9. 13. The product resulting from curing the curable composition of claim
 10. 